What lending requirements will you face?  

We would rent out our current residence once we house hack, but the downside is that the cashflow equation is not the most advantageous (barely + with BP calculator).

I wanted to provide a case study on my time with the company and hopefully provide an unbiased “face based” documentation of my dealings with the organization.In early July 2016 I heard about Clayton Morris, through his BiggerPockets Interview, which led me to the Morris Invest Podcast.

For every $100k you have in appreciation you’re going to face about $30k in additional taxes by making it a rental in California.

IF you owe tax then they cannot assist you except to make sure that you are not over-taxed or asked to face any undue burden in the process.

So for future reference, whats the difference between a squatter and a trespasser and what consequences can they face. the basement is definitely NOT considered a living environment. its just for storage and laundry.

For instance, you could face major legal issues if you accidentally (ignorance is poor defense, especially in the Peoples Republic of Illinois) charge a tenant more than what you were charged plus the state allowed fee.

You would be correct in thinking Zillow or any other mainstream consumer facing platform like that is not the best place... you can get lucky but thats not good thing to bank on.

My opinions are 1) keep my current home as a rental, I can buy the new home with a VA loan put 10% down to keep my mortgage just barely below 28% of our monthly income but now most of our savings are gone or 2) sell my home, buy new with VA loan put 20% down but now with my current saves and what would be left over after the sale I would have over 100k to help fund our business.

Currently, your equity is buying a property that is worth 1.5 times the face value of that equity.